Don’t Forget: 2019 Chicago Seminars

Filed Under: Advice, Misc.

I can’t believe I forgot to write about this earlier. Well, I can, as it’s been a complicated summer here, and this is one of those things each year where I know I’m going, pretty much everyone I know seems to be going, and at some level I think I just assumed that you were all already planning on going as well. Oops.

One of the longest standing annual miles & points “events” is the Chicago Seminars, which has been held at the Holiday Inn in Elk Grove, Illinois (nearish to the Chicago O’Hare Airport) for the past nine years.

Nine years. I’m getting old.

The Chicago Seminars will be returning for a tenth year, and will be held October 18-20, 2019.

Ben and I actually met in-person for the first time at a Chicago Seminars many moons ago, so the event is always covered in nostalgia for me. The fact that Howie Rappaport has this event down to a science so that very little changes year to year probably helps with that. While there are plenty of new folks each year, seeing the same faces in the same format (including the staff at the host hotel) always makes it feel more like a family reunion to me than anything else.

This is an all-volunteer event, with all the proceeds going to charity. The $125 registration fee includes access to all sessions (based on space availability), lunch Saturday and Sunday, along with coffee breaks and the Saturday night Happy Hour.

That being said, if you have dietary restrictions you may want to plan on making alternative meal arrangements (I personally pack like an immigrant grandmother and am happy to share purse almonds or bouillon cubes; the host hotel rooms do have refrigerators), and possibly even going as far as to rent a car. There isn’t much in the area (there is a restaurant on-site with a sports bar style menu, and a Starbucks and a Taco Bell within walking distance), and as of last year Postmates didn’t deliver to the hotel.

Here are the links with all the most important info:

As is traditional for this event, there is a very diverse assortment of speakers spread over two dozen sessions. I generally like to focus on the very beginner sessions, and will be giving a spiel about the basic stuff you need to know before booking your first award.

I’ll also be doing what I expect will be a very poorly-attended Ask Me Anything, as it’s opposite a couple of other great sessions (though I will have an entire suitcase full of amenity kits and airline pajamas to give away as bribes, and may have a special guest 😉 ).

And then I’ll be around to moderate some of the panels on Sunday and answer general questions — it’s typically a very low-key and enjoyable event.

The Chicago Seminars generally attract a good mix of people new to miles and points and savvy veterans, which makes for a fun weekend. We typically have the entire hotel for ourselves, which makes for a cozy event, with lots of great conversations in the bar and hallways. If you haven’t been to an event like this, and can make it to Chicago in a couple of weeks, I highly recommend it! And ten years (10!) is sorta a big deal!

I know many of us are last-minute planners, so hope to see lots of you there!

  1. Went to one and it felt like I was back in high school with everyone huddling around the “cool kids” in the same cliques each night at the bar or during the breakout sessions. If you’re a total noob to the game this seminar might be worth it but for those who’ve been around a while it’s a pass. Unless, of course, you’re one of the blogger fanboys. Hahaha

  2. How fun. I wanted to go about 5 years ago, but couldn’t. It’s cool that it is soo affordable. If you know anything about these social media formed guru events, this is a crazy low price.

  3. How convenient, since I now live in Chicago! Unfortunately I may have a few other commitments that weekend, so I’m wondering if there’s a way to register for just one day?

    In any case, hoping to make it and see you there.

  4. Thank you for this article, Tiffany. A first for me in terms of Chicago Seminars, so I appreciate the high marks.

    I’ll be there. Looking forward!

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